N-(biphenyl-2-yl)-4,6-dichloro-1,3,5-triazin-2-amine | 107918-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(biphenyl-2-yl)-4,6-dichloro-1,3,5-triazin-2-amine
• 英文别名: 6-(biphenyl-2-ylamino)-2,4-dichloro-1,3,5-triazine；biphenyl-2-yl-(dichloro-[1,3,5]triazin-2-yl)-amine；Biphenyl-2-yl-(dichlor-[1,3,5]triazin-2-yl)-amin；1,3,5-Triazin-2-amine, 4,6-dichloro-N-(2-biphenyl)-；4,6-dichloro-N-(2-phenylphenyl)-1,3,5-triazin-2-amine
• CAS: 107918-32-1
• 化学式: C₁₅H₁₀Cl₂N₄
• 分子量: 317.177
• InChiKey: MBVGSAIXNWXZSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(biphenyl-2-yl)-4,6-dichloro-1,3,5-triazin-2-amine 、 1H-吲哚-6-甲胺 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 N2-((1H-indol-6-yl)methyl)-N4-([1,1'-biphenyl]-2-yl)-6-chloro-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Discovery and SAR of a series of 4,6-diamino-1,3,5-triazin-2-ol as novel non-nucleoside reverse transcriptase inhibitors of HIV-1

  摘要：

  The discovery and SAR study of a series of 4,6-diamino-1,3,5-triazin-2-ol compounds as novel HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) are reported. The lead compounds in this series showed excellent activity against wild-type and drug-resistant RT enzymes and viral strains. In addition, compounds from this series demonstrated favorable pharmacokinetic profile in rat. A preliminary modeling study was conducted to understand the binding mode of this series of compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.034
• 作为产物：
  描述：

  三聚氯氰 、 2-氨基联苯 生成 N-(biphenyl-2-yl)-4,6-dichloro-1,3,5-triazin-2-amine
  参考文献：
  名称：

  芳基氨基-1,3,5-三嗪溶液的合成、结构和动力学行为

  摘要：

  十个不对称取代的芳基氨基-1,3,5-三嗪合成并通过动态核磁共振光谱研究。受阻旋转的自由能 ΔG≠? 在 59–77 kJ mol− 1 范围内。使用差模 NOE NMR 实验，证明了主要和次要旋转异构体的结构。进行了 DFT B3LYP/6-31G* 计算。计算出的旋转障碍与通过线形分析获得的实验值之间的差异小于 7.6 kJ mol-1。旋转势垒的高度在 18 kJ mol-1 范围内变化，具体取决于三嗪环中的取代基。

  DOI：

  10.1007/s11172-006-0135-0

文献信息

• Synthesis, structure, and dynamic behavior in solution of arylamino-1,3,5-triazines
  作者：P. A. Belyakov、A. V. Shastin、Yu. A. Strelenko

  DOI：10.1007/s11172-006-0135-0

  日期：2005.10

  3,5-triazines were synthesized and studied by dynamic NMR spectroscopy. The free energies of the hindered rotation ΔG≠?are in 59–77 kJ mol− 1 range. Using difference-mode NOE NMR experiments, the structures of the major and minor rotation isomers were proved. The DFT B3LYP/6-31G* calculations were performed. The difference between the calculated rotation barriers and the experimental values obtained

  十个不对称取代的芳基氨基-1,3,5-三嗪合成并通过动态核磁共振光谱研究。受阻旋转的自由能 ΔG≠? 在 59–77 kJ mol− 1 范围内。使用差模 NOE NMR 实验，证明了主要和次要旋转异构体的结构。进行了 DFT B3LYP/6-31G* 计算。计算出的旋转障碍与通过线形分析获得的实验值之间的差异小于 7.6 kJ mol-1。旋转势垒的高度在 18 kJ mol-1 范围内变化，具体取决于三嗪环中的取代基。
• Discovery and SAR of a series of 4,6-diamino-1,3,5-triazin-2-ol as novel non-nucleoside reverse transcriptase inhibitors of HIV-1
  作者：Bin Liu、Younghee Lee、Jinming Zou、H. Michael Petrassi、Rhoda W. Joseph、Wenchun Chao、Enrique L. Michelotti、Marina Bukhtiyarova、Eric B. Springman、Bruce D. Dorsey

  DOI：10.1016/j.bmcl.2010.09.034

  日期：2010.11

  The discovery and SAR study of a series of 4,6-diamino-1,3,5-triazin-2-ol compounds as novel HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) are reported. The lead compounds in this series showed excellent activity against wild-type and drug-resistant RT enzymes and viral strains. In addition, compounds from this series demonstrated favorable pharmacokinetic profile in rat. A preliminary modeling study was conducted to understand the binding mode of this series of compounds. (C) 2010 Elsevier Ltd. All rights reserved.